According to the present invention, a process is provided for reacting an aniline compound with a lactone. This reaction is referred to herein as an "alkylation" reaction. The term "alkylation" is thus used herein to refer to an addition reaction between an aniline and a lactone.
The compounds prepared in accordance with the process of the present invention are especially useful as fungicides.
Commonly assigned U.S. Pat. No. 3,933,860 discloses the preparation of lactone-substituted compounds wherein in a first step the following reaction is carried out: ##STR1## As can be seen from the examples in U.S. Pat. No. 3,933,860, the aniline reaction is carried out in the absence of water. Thus, in Example 1, 3,4-dichlorobenzeneamine (which may also be called 3,4-dichloroaniline) is reacted with 3-bromotetrahydro-2-oxofuran (which may also be called alpha-bromo-gamma-butyrolactone) at 110.degree. to 145.degree. C. to give a solid mixture of about equimolar amounts of 3,4-dichlorobenzeneamine hydrobromide salt and N-(tetrahydro-2-oxo-3-furanyl)3,4-dichlorobenzeneamine [which may also be called 3-(N-3,4-dichlorophenylamino)-gamma-butyrolactone]. The mixture thus obtained was treated with dichloromethane and filtered to separate the salt as a solid. The filtrate was evaporated to thereby remove the dichloromethane and yield the desired aniline-lactone reaction product.
In Example 2 of U.S. Pat. No. 3,933,860, 0.1 mol 2,6-dimethylbenzeneamine, 0.1 mol 3-bromotetrahydro-2-oxofuran, 0.1 mol sodium carbonate and 150 ml dimethylformamide were heated as a slurry to 125.degree.-140.degree. C. The reaction time was 21 hours. After the reaction was complete, the reaction mixture was diluted with water at room temperature and then extracted with benzene to remove the desired aniline-lactone product. The organic phase, that is, the benzene phase, was processed to separate the aniline-lactone product from the benzene phase.